Posts Tagged crossdressing

Two guys, one vegetable

A few weeks ago I got this message on one of my sites:
“Officially straight, but had a couple of discreet bi meets, and after more. Ideally with a younger guy. Available most mornings, but cannot accommodate. Have a thing for crossdress if that interests you at all? Be great to hear back if interested, and we can message and exchange pics first.”

Repeating my mantra of “I’ll try anything once…”, I got back in touch and told him I was available some mornings depending on Uni, that I can accommodate, and that I was happy to dress up for him as long as he provided the clothes. Photos were exchanged and eventually, when conflicting work and study schedules were resolved, he came to mine last Tuesday for some fun.

I was pleasantly surprised when I opened the door; he was actually really good looking in person and his body was more toned (not that he was topless on the doorstep, you understand, the neighbours wouldn’t approve). I let him and and showed him to the bedroom, while I went into the bathroom to change into the clothes he handed me when he arrived. Fully kitted out in tights, a black and pink bra and a vest top (which actually all fit really well), I went into my room to find him naked on my bed, and as we’d described in our email exchanges, I set to work sucking him off straight away.

He came after less than three minutes, like he thought he would, so while he was recharging he reached down into his bag and pulled out – not a sex toy, as I was expecting – a carrot. I shit you not, a carrot. “Work kept me really busy, so I couldn’t get everything I wanted…”

But, in for a penny, in for a pound(ing), I lay back and relaxed as he put a condom on it and lubed me up and in it went.

Carrots… they’re not as smooth as you might think. This one was fairly straight as far as carrots go (I’ve taken to evaluating the shapes of them whenever I’m in the supermarket now and thinking thank Christ it wasn’t that one) but still,their surface is quite rough and even through the condom I could feel that. After a few minutes he pulled it out and I expected him to fuck me, but no, he couldn’t get it up, so I decided to give him a helping hand (read: helping mouth). He still didn’t get hard  for ages, and then when he did it was only to cum (again) and then he got soft again. Very disappointing.

So to cut a long story short, I more or less just finished myself off and kicked him out. I couldn’t help but think, maybe you are just straight after all – so why bother finding a guy who’s going to dress up for you? Still, it was an experience and I don’t know that I would be very resistant to crossdressing again (There’s a seemingly endless subculture of self-described “traps” and/or “fembois” on Tumblr and a lot of them aren’t bad looking at all, at least in my view!). Who knows?

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Submissive Sunday: My First Sex Party, or Meeting Bondage Girl

Three guesses where this person lives!!

Last summer I was outside camping with some friends. We were almost in the middle of nowhere, surrounded by big trees right next to our tent and next to an open field. Somehow I ended up in my friend’s tent (which is a whole other story to write about) and we had barely fallen asleep when the wind started kicking in. Normally I’m not afraid of thunderstorms but this one was right over us. The lightning came right along with some earth shattering thunder.

It was like Noah’s perfect day to take his new ark out for a ride – Armageddon LIVE! – and I think for the first time in my life I was really aware that nature is so much more powerful than we humans and that if we don’t take good care of ourselves we could end up dead…

“But I don’t want to die!!”, I thought to myself followed by the first next thought that came to my mind….”I need to have more sex!!!”. I don’t know if you ever had the feeling that this might be IT. But I figured that the “I need to have more sex” thing was definitely something that needed to be realized ASAP!

So obviously we all didn’t die, otherwise I wouldn’t be able to write this story but I didn’t forget about my “God’s given ‘vision’ ”

Since I am so not into the whole “let’s go out dancing, get drunk and find someone to have sex with”-thing and I am also not really into having sex as a straight woman – I was hunting around for places where my queer self would be much appreciated AND I could have sex (also, there is a slightly higher chance of running into men in woman’s underwear at queer sex parties than in an ordinary club ;-))

Luckily I live in one the the world’s most artsy and colourful cities, so there are countless possibilities to find a good sex party: straight, lesbian, gay, queer, BDSM, trans*, role play, with and without playing dirty (maybe the term “golden shower” rings a bell) leather fetish….we even have several locations which offer special “playgrounds”, meaning you find cages, crosses, stretching banks as well as whips, riding crops and bondage gear. As I always say: we live in paradise. It’s right there in front of your eyes, you just have to look around and view it. (As Willy Wonka likes to sing….I have a chocolate fetish by the way, but then who doesn’t ;-))

Off I went to my first sex party which luckily somehow was almost right next to my place, so even as I wanted to chicken out there were no excuses like “but it’s too far, I’m too tired, it’s raining”. I decided to go for a “no underwear, nylons, mini-skirt and minor-see-through shirt along some with heels” – outfit.

It was a party for women, lesbians and trans* which also offered a short bondage workshop in the beginning – something that I  always have been curious about.

The place itself looked like a “playground for adults”. As I walked down the stairs I found myself in the arousing world of leather swings, cages and gynaecologist chairs – so hot! Very happy about this newly found universe in the city, I was literally gliding upstairs, flying by the bar straight into another room in the backside of the club.

Comfy, wide imitation leather couches were waiting for their horny guests.

The woman who was offering the bondage workshop gave the female crowd an overview about the basic rules for tying someone up nicely and even more important: safely! (Note: always have a pair of scissors handy.) I was so excited about learning about different ropes and knots to fiercely dominate and tie up the next person who would be remotely submissive, but after several demonstrations of different knots (and a very long working day) my brain was one big knot itself and couldn’t remember anything that it just had been taught. So there went my fantasy…

So I bravely volunteered to play the submissive part as we got to practise on each other. In walks – as I like to call her – Bondage Girl. Tall, athletic body, short blond hair (and a very stylish haircut! I am a sucker for stylish haircuts!), green eyes…”So…you want to be tied up?!”…rope in her hands…

I huddled up in my short skirt and nylons thinking: “I’m not wearing a thong…now everyone is gonna see my…ah…right! Sex Party…! Exhibtionist mode on…!” (not that it’s ever off)-

Bondage Girl straightens out the rope… it gently glides around my ankles winding its way up my each leg like a snail… smoothly moving the soft nylon on my skin…

“Shall I go on and tie you up even more? I am in the mood to experiment…” Experiment away!

The rope continues its journey around my hands which are now safely secured in a praying position in front of my chest. Each time she makes a knot she pulls the rope gently but firmly, leaving no doubt that she’s in control. She takes my shackled hands, puts them behind my head and starts sliding the rope around my chest…there is no way to move my hand from the back of my head. She loops the rope around each breast continuing making smaller knots on my sternum…then she pulls the whole art work on my sternum towards her…It’s like 10 pairs of hands touching you everywhere of your body, luring you with the sweet gentle touch of a lover and leaving you with the feeling of being someone’s prey…

I never thought I would enjoy receiving bondage, leaving me wanting more. In my personal life and in my life as woman who runs her own business I am quite the doer. So of course it first felt like the obvious and natural thing to be the one to “do” (give) bondage to a play partner. WRONG! It was somehow not only arousing but also very relaxing to for one moment NOT be the one to “pull the strings”.

Guess you never know until you try 😉

After this night I ran into the woman who was offering the bondage workshop during a female porn award party (GOD! I love my colourful artsy hometown!) and I kind of started seeing her. Since she obviously is into giving bondage it naturally led to being “tied up” during another sex party where I also had a fierce “foreplay” with a gorgeous trans* in woman’s underwear, suspenders, nylons and high heels…but that’s another story…

In case you are getting curious yourself about going to a sex party – here are some tips.

Things you want to check before going to a sex party and while you are there:

– Check with people who already have been there if it is a safe place for you to be there – what were their experiences like? (I did ask the owner and well known sex-positive activist in my favourite sex shop for women and trans* as well as  people from the queer community)

– Know what you like or would like to experience and were your borders are. Being tiet up might be a lot of pleasure for one person but sheer horror for another.

– ALWAYS PLAY SAFE!!!!! If you are going to a sex party there should be free access to condoms, dental dams and gloves as well as lubricant. If you have small hands like I do it might be a good idea to bring your own gloves in a smaller size since I mostly find gloves starting at a medium size at these parties. Of course this works, too, but if you are finger fucking someone – especially guys – the gloves tend to wrinkle up which can be a bit unpleasant for the other person. Also for fisting it’s important that the gloves fit perfectly well.

– For sanitary purposes there should be disinfection spray and wipes. All surfaces at the party should be able to be cleaned and disinfected. The playground should look and be left clean.

– The rules of the sex party should be printed out and visible to everyone. Read them! Normally the door men or woman or someone who has already been there will explain these rules to you and give you a tour through the location.

– Always check if it is ok to watch a sex scene. Of course you don’t just walk up to someone and ask during their play but normally people give hand signs or let you know if they don’t want you to watch. It’s always good to ask when you arrive at a party what the rules about watching a scene are.

–  If you are hearing the words “Help me, please help me!!!” it’s not necessarily a reason to rush over and “free” the other person. Especially at BDSM parties this can be part of the play. However each party has code words to ensure the safety. I mostly find the code words: green, yellow and red. Red usually is the term for “stop”. Make sure to know what the code words are BEFORE becoming intimate with someone. Talk to the other person about your code word for “stop” and know theirs.

– Get to know the person(s) you will have sex with BEFORE the actions starts. A good and healthy minded play partner will ask for your borders (“is there anything that you don’t want me to do?”) and might even check with you during the action when unsure. Since I am not of the quiet kind I had a very cute play partner ask “Is it ok what I am doing?” couple of times during our night of fun before s/he knew for sure I was (very!!!) fine 😉 For example: I like to be tied up and spanked but you don’t want the person to grab my feet – Might seem illogical, but it gives you an idea.

– If the person wants you to do something you haven’t tried before and you are curious but inexperienced: Let them know! They might be fine with it and teach you something new and exciting! However if you are not up for this particular new practise, just say “no”.

– The most important thing someone taught me at a sex party was: “You have to learn to say NO.” If someone wants to have sex with you but you don’t, it doesn’t mean that you have to say YES because you are at a sex party. NO it is! Also, if they are into something that crosses your healthy borders and you don’t feel comfortable with: NO!

Having sex is very intimate and you open yourself up to someone because you trust them. Always make sure you are and feel safe otherwise you will be left with some scars (not only physically but mentally) and you might end up paying a lot of money for a good therapist.

– Stay clean! Sex parties are definitely not the place to get drunk or take drugs of any kind. You want to be your sober self who is aware of what you are doing and what you are receiving. Though there are quite some drugs out there that can intensify the pleasures of sex I certainly would not take them with someone I don’t know.

– Be yourself! Be open about what you like. Dress like you feel like. One of the questions I get the most is: What to people wear during a sex party. Well, that depends on the party. If it’s a BDSM party I see a lot of leather gear. At a party for woman/lesbian I found a lot of tank tops and jeans, at a queer party I found people dressing from casual to half-naked-pink-butterfly-elf with glitter. Some are standing by the bar in their underwear, others have see-through tops, I like to go for short dresses and skirts without underwear and nylons…so it really depends on what you like! Don’t dress as someone you are not, try to find a way to express yourself through your outfit.

COME as you are 😉

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Submissive Sunday: Don’t dream it – be it: Part 1 – Getting inspired

Keep an eye out for part two next week. There are some really interesting-sounding things coming up on Sundays, and if you feel like putting pen to paper (so to speak) drop me a like at triplexdexxx@gmail.com!

By “Magenta”

When I was about 15 years old I consciously started looking for guys on the street. Whenever I found someone that caught my eye my friends would always say “but he’s OBVIOUSLY gay! It’s written on his forehead!”
I went to a posh private school so I was surrounded by uptight teenagers wearing Ralph Lauren Polo Shirts, who were raised by there old-fashioned parents whereas I was living at a children’s home at the time. It was pretty much “Little Punkrock Girl vs. The establishment” person.
At the same time I also started fancying several singers of different bands who interestingly enough were all into wearing eye liner, putting some nail polish on and even going on stage in suspenders (Think of Ville Valo, singer of HIM in the video “Join me”. Ooooooft!).
But since all my school mates were brought up “nice and clean” there was zero possibilty of someone talking to me saying “oh, so you are…bi-sexual…lesbian….queer.” I think at the time I didn’t even know some of these words existed. Also it was the early 90’s so we didn’t have facebook, gay websites, queer blogs…nothing…even worse: NO INTERNET AT ALL!!!  This also meant: No googling your questions, key words or anything. (And no free porn either! How did I manage too survive?!!)
Then my openly gay music teacher thought that it might be a good idea for our class to perform “The Rocky Horror Picture Show” – The queer “Musical Extravaganza” which is all about stripping down your acquired limitations of how you express your sexuality and actually expressing….being what you dream about. To underline this theme there is the catchy song line “Don’t dream it – Be it” which gets repeated over and over in the end. “Be it” also includes openly coming out as gay, not identifying with your birth-gender aka being genderqueer and giving a crap whether your underwear should exclusively be worn by women.
So off we went to watch the whole thing on the school’s TV (I don’t know if that is actually legal for underage kids but thank GOD we did!).  Each of us got to choose a role afterwards. Since sadly I am in lack of a biological penis (luckily I now own a very pretty strap on version that expresses my male ego as well as matching my body colour)  I could not portray the part of the adorable, smokin’ Frank n Furter – the “Sweet Transvestite from transsexual Transilvania”. So my teacher gave me the role of Magenta – the loud, queer and crazy lunatic with smokey eyes, wearing a very short maids dress, showing off her suspenders (you might have noticed that I have a nylon fetish by now).
One of my best male friends P.  (think: a young Jude Law) ended up in a chair which we put on top of the teacher’s desk.
So far so good. Luckily I somehow had my suspenders with me, so we put my friend P. in them and of course I couldn’t help it putting some mascara and eyeliner on him. Think Jude Law in drag! Ooooooft!
3 Minutes later P. was up on the chair, on the teacher’s desk ready to perform as Frank n Furter, while my gay music teacher was giving instructions.
I will cherish this moment forever…
Suddenly the door to the classroom swings open and in paces the neat principle in his clean buttoned up suit.
SILENCE
About 10 Students were standing around looking a bit befuddled, the TV was showing a still frame of Frank n Furter and 2 of my best male friends were in underpants, one of them up on the teacher’s desk with make up and in women’s underwear…with the gay music teacher right next to their sides for the “final touches” 😉
I think my music teacher was very lucky he didn’t get suspended given the fact that we all were underage.
And sadly somehow we never got to perform the Rocky Horror Show at our posh and expensive little private school…Strange…(just kidding)  But luckily we somehow all got to see “The Rocky Horror Show” live one stange while they were performing in my hometown.
Of course me and my 2 male friends got all dragged-up for the event: I leant them my suspenders and I got to wear my 12cm high plateau boots with my latex pants and my matching latex corset. So I linked arms with 2 hot guys in suspenders and make up – one to the left, one to the right and we felt like super-queer-glitter-rock-star-transvestites from transsexual Transylvania as we were strutting through the main entrance….
Up until this day I believe the hole “Rocky Horror experience” opened my eyes, my heart and other body parts to the queer universe of being your shiny-rainbow-glitter-self.
Weirdly enough this experience was then followed by almost 8 years living as a straight woman before I “came out” to myself.
(Darn you universe! Trapped in a female body when I want to live as a gay guy. But hey… the boobs are great!)
Also people telling me “but you will never find a guy who dresses in woman’s underwear who wants to have sex with a woman!” really didn’t help.
Well guess what: I did! Not only once, but twice during the last couple of months…and I will keep on finding them thanks to the power of the glitter-universe and my magic wand (aka  “strap on” in the world of queer)…so bend over boyfriends, female lovers and genderfucks….for there will be part 2 of this story of how, where and when I actually got to “be it”….
PS: In case you are wondering: Today my friend P. is a well paid medical doctor, wearing a Rolex watch and starchy shirts and he is very straight (A ZERO on the Kinsey scale if that rings a bell. If not try it on Google. It’s 2012 and you have access to the internet you lucky bitches, butches, dykes and divas!)

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Flashback Friday – Crossdressers in the Cupboard

The youth group I mentioned in last week’s Flashback Friday turned out to be a really fun thing to go along to on a regular basis and though I really didn’t appreciate it at the time, looking back I can see that I had a very good (I won’t say “healthy”) sex life for a sixteen year old. The second residential weekend I went on with them involved once again, a bunch of LGBT young people with hormones flying everywhere staying in an isolated house in the countryside. Sounds like the opening to a really shit and predictable horror film, doesn’t it? It wasn’t.

I think, if I remember rightly, we were there to film an an awareness/coming out/ anti-LGBT-phobia type DVD for the health service but most of the weekend was spent just having fun in that way that teenagers consistently will. On what I assume was the Saturday night we had a drag workshop and so I ended up in a dress and make-up for the first time in my life (but definitely not the last!). There were very few boys there that weekend, I can only think of a few, but one of the others was a painfully flamboyant boy who at the time was called K but has since changed his name to L, so since we already have one story about a K recently we’ll stick with L. We were all a bit over-excited, running around this house, and L and I – whether by design or accident I’m not sure – ended up alone in one of the bedrooms. Against a wall. Ahem. We sensibly decided though that a bedroom anyone could walk into at any time probably wasn’t the safest of places to be at it so we ended up down the corridor in the boiler cupboard. Yep, I’m that classy. (What do you expect from someone whose first sexual encounter was at a church?)

The advantages of wearing dresses and skirts became obvious to me for the first time that night, in that you have almost unimpeded access to everything you need to have access to to have sex without having to actually get undressed in a cold boiler room in the middle of winter.

And wow, I’m all for sexual preferences, but to say that L was a completely submissive bottom bitch doesn’t even begin to sum it up. Had I been more experienced and adventurous I probably could have done just about anything to him and not only would he have accepted it, he’d have gotten off on it. It took a couple of attempts since I’d no idea what the hell I was doing really, and fell out a couple of times, but in the end we got there and I properly fucked someone for the first time. It felt great being on top, dominating, sort of powerful. Because I’m a far cry from being an Alpha-male, it’s a rare occasion I can find someone passive enough for me to completely take advantage of, so I have to enjoy it while I can, and I’m sure that it all stems from this one experience of fucking a boy in a dress in the cupboard.

After I moved to my current city I never really heard from him for a few years, though I got updates on his ever-growing level of campness from a mutual friend who sees him out and about sometimes. I ran into him a few weeks ago in a club on Barman night (I saw a lot of people from years ago that night, it was a bit disconcerting) but we have nothing to talk to one another about so we simply didn’t.

There we go, another tale from the archives. Submissive Sunday coming up, I’ve already had a few stories in and if everyone that has offered to write me a guest post follows through we should have some really interesting stuff coming in the next few weeks!

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